The 1099 question turns on how the payee is taxed. Sole proprietors, partnerships and most LLCs get one. S corps and C corps do not, with two exceptions worth knowing.
The W-9 is what a contractor gives you before work starts. The 1099 is what you give them and the IRS after year end. How the two connect, and where businesses slip.
Contractor mistakes surface in January, not when you pay. Classification, payment records, and the habits that keep year-end filing from becoming a scramble.
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